Enantiomerically pure 4-methyl- and 1,4-dimethyl-bicyclo[3.2.0]hept-3-en-6-ols and ones by microbial redox

Chemistry Letters

Volumn , Issue 7, 1996, Pages 511-512

  Fantin, Giancarlo ^a   Fogagnolo, Marco ^a   Marotta, Emanuela ^b   Medici, Alessandro ^a   Pedrini, Paola ^a   Righi, Paolo ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030507588     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.511     Document Type: Article

References (11)

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3. E. Marotta, M. Medici, P. Righi, and G. Rosini, J. Org. Chem., 59, 7529 (1994).
4. G. Fantin, M. Fogagnolo, A. Medici, P. Pedrini, E. Marotta, M. Monti, and P. Righi, Tetrahedron: Asymm., 6, 2319 (1995).
5. M. J. Dawson, G. C. Lawrence, G. Lilley, M. Todd, D. Noble, S. M. Green, S. M. Roberts, T. W. Wallace, R. F. Newton, M. C. Carter, P. Hallett, J. Paton, D. P. Reynolds and S. Young, J. Chem. Soc. Perkin Trans. I , 1983, 2119.
6. a) G.Fantin, M. Fogagnolo, A. Medici, P. Pedrini, S. Poli, and M.Sinigaglia, Tetrahedron Lett., 34, 883 (1993).
7. b) G. Fantin, M. Fogagnolo, A. Medici, P. Pedrini, S. Poli, and F. Gardini, Tetrahedron Asymm., 4, 1607 (1993).
8. G. Fantin, M. Fogagnolo, A. Medici, P. Pedrini, and G. Rosini, Tetrahedron: Asymm., 5, 1635 (1994).
9. Enantiomer separation was obtained on Megadex 5 column (25 m × 0.25 mm) containing n-pentyl dimethyl β-cyclodextrin in OV 1701 from Mega s.n.c.: carrier gas: helium 0.8 atm; temp. 100-200°C (1.5 °C/min). Retention time in min:(-)-1R,5S-1a, 9.12; (+)-1S,5R-1a, 9.44; (-)-1R,5S,6S-endo-2a(as acetyl derivative), 14.10; (+)-1S,5R,6R-endo-2a (as acetyl derivative), 14.51; (-)-1R,5S,6R-exo-3a, 14.15; (+)-1S,5A,6S-exo-3a, 14.53; (-)-1R,5S-1b, 7.09; (+)-1S,5A-1b, 7.39; (-)-1R,5S,6S-endo-2b, 10.43; (+)-1S,5R,6R-endo-2b, 10.78; (-)-1R,5S,6R-exo-3b, 11.23; (+)-1S,5R,6S-exo-3b, 11.59.
10. E.Marotta, I. Pagani, P. Righi, G. Rosini, V. Bertolasi, and A. Medici, Tetrahedron: Asymm., 6, 2319 (1995).
11. W. P. Griffith, and S. V.Ley, Aldrichim. Acta , 23, 13 (1990).